Sodium Iodide → 5-Chloro-3-[(phenylthio)methyl]-1,2,4-thiadiazole

HRID 346491

반응식

HRID 346491 반응식
[Na+].[I-].[Cl:3][C:4]1[S:8][N:7]=[C:6]([CH2:9]Cl)[N:5]=1.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.CCOC(C)=O.O>[Cl:3][C:4]1[S:8][N:7]=[C:6]([CH2:9][S:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=1

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 7969ThiophenolHCID 10340Sodium CarbonateHCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazole

생성물 1

HCID 210814585-Chloro-3-[(phenylthio)methyl]-1,2,4-thiadiazole

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

1.05 eq of NaI were dissolved in dry acetone. 1 eq of 5-chloro-3-(chloromethyl)-1,2,4-thiadiazole, 1.03 eq of the thiophenol and 1 eq of Na2CO3 were added and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with EtOAc and water. The organic phase was washed with an aqueous solution of Na2SO3 (sat), dried over MgSO4 and evaporated in vacuo. Preparative HPLC purification gave the 5-chloro-3-[(phenylthio)methyl]-1,2,4-thiadiazole. This was subsequently dissolved in 95% ethanol and conc. NH3 (aq) was added. In some cases acetonitrile was added in order to completely dissolve the starting material. The mixture was transferred to a microwave tube and run in the microwave at 150° C. for 5 min. the reaction was quenched with water and the desired 3-arylthiomethyl-5-amino-1,2,4-thiadiazole worked up and purified using standard procedures.

후처리

  1. washThe organic phase was washed with an aqueous solution of Na2SO3 (sat)
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customPreparative HPLC purification

출처 및 근거

ORD 기록
ord-111ed844a99d4345a191b2cd24b48c9b
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173030B2

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